# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1FNaAA
_audit_block_doi                 10.5517/ccdc.csd.cc23dlx1
_database_code_depnum_ccdc_archive 'CCDC 1948533'
loop_
_audit_author_name
_audit_author_address
'Jiaxi Liu'
;Jilin University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;
_audit_creation_date             2019-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 F O2'
_chemical_formula_sum            'C13 H9 F O2'
_chemical_formula_weight         216.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.7599(8)
_cell_length_b                   3.7695(4)
_cell_length_c                   38.685(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.899(4)
_cell_angle_gamma                90
_cell_volume                     983.46(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5513
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.59
_cell_measurement_theta_min      3.02
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            10763
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.596
_diffrn_reflns_theta_min         3.020
_diffrn_ambient_temperature      99.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2339
_reflns_number_total             2755
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+0.7258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1436
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.30371(14) 0.3950(3) 0.64823(2) 0.0224(2) Uani 1 1 d . . . . .
O002 O 0.05494(18) 0.8351(4) 0.54093(3) 0.0265(3) Uani 1 1 d . . . . .
O003 O 0.24119(19) 0.8659(4) 0.49533(3) 0.0273(3) Uani 1 1 d . . . . .
C004 C 0.6204(2) 0.1523(4) 0.66206(4) 0.0148(3) Uani 1 1 d . . . . .
C005 C 0.8114(2) 0.0663(4) 0.65113(4) 0.0151(3) Uani 1 1 d . . . . .
C006 C 0.5243(2) 0.3832(4) 0.60369(4) 0.0151(3) Uani 1 1 d . . . . .
C007 C 0.4852(2) 0.3099(4) 0.63732(4) 0.0151(3) Uani 1 1 d . . . . .
C008 C 0.2169(2) 0.7839(4) 0.52661(4) 0.0171(3) Uani 1 1 d . . . . .
C009 C 0.7170(2) 0.2929(4) 0.59354(4) 0.0157(3) Uani 1 1 d . . . . .
C00G C 0.7120(3) -0.0715(5) 0.71921(4) 0.0221(3) Uani 1 1 d . . . . .
C00C C 0.3855(2) 0.6245(4) 0.54699(4) 0.0185(3) Uani 1 1 d . . . . .
C00A C 0.8549(2) 0.1412(4) 0.61642(4) 0.0164(3) Uani 1 1 d . . . . .
C00D C 0.9509(2) -0.0894(4) 0.67553(4) 0.0185(3) Uani 1 1 d . . . . .
C00E C 0.5724(2) 0.0794(4) 0.69639(4) 0.0195(3) Uani 1 1 d . . . . .
C00B C 0.3702(2) 0.5403(4) 0.58028(4) 0.0163(3) Uani 1 1 d . . . . .
C00F C 0.9024(3) -0.1541(4) 0.70874(4) 0.0212(3) Uani 1 1 d . . . . .
H009 H 0.756(3) 0.340(5) 0.5698(5) 0.017(5) Uiso 1 1 d . . . . .
H00A H 0.983(3) 0.071(5) 0.6088(5) 0.018(5) Uiso 1 1 d . . . . .
H00D H 1.081(3) -0.162(6) 0.6672(5) 0.027(5) Uiso 1 1 d . . . . .
H00B H 0.252(3) 0.582(6) 0.5912(5) 0.021(5) Uiso 1 1 d . . . . .
H00C H 0.506(3) 0.585(6) 0.5353(5) 0.026(5) Uiso 1 1 d . . . . .
H00E H 0.440(3) 0.129(6) 0.7034(5) 0.026(5) Uiso 1 1 d . . . . .
H00G H 0.678(3) -0.121(6) 0.7428(6) 0.029(6) Uiso 1 1 d . . . . .
H00F H 0.998(3) -0.256(6) 0.7252(5) 0.028(5) Uiso 1 1 d . . . . .
H003 H 0.099(7) 0.992(13) 0.4797(10) 0.136(17) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C007 1.3623(16) . ?
O002 C008 1.2747(19) . ?
O003 C008 1.2704(19) . ?
O003 H003 1.20(5) . ?
C004 C005 1.423(2) . ?
C004 C007 1.409(2) . ?
C004 C00E 1.415(2) . ?
C005 C00A 1.422(2) . ?
C005 C00D 1.416(2) . ?
C006 C007 1.373(2) . ?
C006 C009 1.427(2) . ?
C006 C00B 1.459(2) . ?
C008 C00C 1.470(2) . ?
C009 C00A 1.367(2) . ?
C009 H009 0.987(19) . ?
C00G C00E 1.371(2) . ?
C00G C00F 1.410(2) . ?
C00G H00G 0.97(2) . ?
C00C C00B 1.337(2) . ?
C00C H00C 0.97(2) . ?
C00A H00A 0.97(2) . ?
C00D C00F 1.369(2) . ?
C00D H00D 0.99(2) . ?
C00E H00E 0.97(2) . ?
C00B H00B 0.94(2) . ?
C00F H00F 0.96(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 O003 H003 115.2(19) . . ?
C007 C004 C005 117.01(13) . . ?
C007 C004 C00E 122.65(14) . . ?
C00E C004 C005 120.34(14) . . ?
C00A C005 C004 119.03(13) . . ?
C00D C005 C004 118.24(14) . . ?
C00D C005 C00A 122.73(14) . . ?
C007 C006 C009 116.81(13) . . ?
C007 C006 C00B 119.63(14) . . ?
C009 C006 C00B 123.55(13) . . ?
F001 C007 C004 116.43(13) . . ?
F001 C007 C006 118.79(13) . . ?
C006 C007 C004 124.78(14) . . ?
O002 C008 C00C 119.10(14) . . ?
O003 C008 O002 123.22(14) . . ?
O003 C008 C00C 117.68(14) . . ?
C006 C009 H009 121.2(11) . . ?
C00A C009 C006 121.12(14) . . ?
C00A C009 H009 117.7(12) . . ?
C00E C00G C00F 120.54(15) . . ?
C00E C00G H00G 119.3(14) . . ?
C00F C00G H00G 120.1(13) . . ?
C008 C00C H00C 117.3(13) . . ?
C00B C00C C008 120.37(15) . . ?
C00B C00C H00C 122.3(13) . . ?
C005 C00A H00A 118.6(12) . . ?
C009 C00A C005 121.24(14) . . ?
C009 C00A H00A 120.0(12) . . ?
C005 C00D H00D 117.4(12) . . ?
C00F C00D C005 120.54(15) . . ?
C00F C00D H00D 122.0(12) . . ?
C004 C00E H00E 120.0(13) . . ?
C00G C00E C004 119.55(15) . . ?
C00G C00E H00E 120.4(13) . . ?
C006 C00B H00B 112.5(12) . . ?
C00C C00B C006 126.54(15) . . ?
C00C C00B H00B 121.0(12) . . ?
C00G C00F H00F 119.1(13) . . ?
C00D C00F C00G 120.79(15) . . ?
C00D C00F H00F 120.2(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6BrNaAA
_audit_block_doi                 10.5517/ccdc.csd.cc23dp4c
_database_code_depnum_ccdc_archive 'CCDC 1948602'
loop_
_audit_author_name
_audit_author_address
'Jiaxi Liu'
;Jilin University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;
_audit_creation_date             2019-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Br O2'
_chemical_formula_sum            'C13 H9 Br O2'
_chemical_formula_weight         277.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9738(2)
_cell_length_b                   6.2790(4)
_cell_length_c                   21.6685(13)
_cell_angle_alpha                97.582(2)
_cell_angle_beta                 93.911(2)
_cell_angle_gamma                92.391(2)
_cell_volume                     533.98(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8412
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.79
_cell_measurement_theta_min      3.56
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.828
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10407
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         2.853
_diffrn_ambient_temperature      293.76
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1950
_reflns_number_total             2076
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.313
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2076
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.2851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1009
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.35993(8) 0.16593(5) 0.44453(2) 0.04760(16) Uani 1 1 d . . . . .
C1 C 0.0988(7) 0.2321(5) 0.32384(14) 0.0351(6) Uani 1 1 d . . . . .
O2 O -0.8201(9) 0.7552(5) -0.00751(12) 0.0653(8) Uani 1 1 d . . . . .
O4 O -0.8713(7) 0.9912(4) 0.07670(11) 0.0559(7) Uani 1 1 d . . . . .
C5 C -0.1674(7) 0.5592(4) 0.29986(13) 0.0311(5) Uani 1 1 d . . . . .
C6 C 0.1513(7) 0.3245(5) 0.38461(14) 0.0343(6) Uani 1 1 d . . . . .
C7 C 0.0528(8) 0.5324(5) 0.40531(14) 0.0387(6) Uani 1 1 d . . . . .
C8 C -0.1253(8) 0.2631(5) 0.21594(14) 0.0377(6) Uani 1 1 d . . . . .
C9 C -0.1041(8) 0.6453(5) 0.36334(14) 0.0371(6) Uani 1 1 d . . . . .
C10 C -0.0624(7) 0.3489(4) 0.27982(13) 0.0308(5) Uani 1 1 d . . . . .
C11 C -0.2816(8) 0.3773(5) 0.17441(14) 0.0383(6) Uani 1 1 d . . . . .
C12 C -0.5508(8) 0.7164(5) 0.15017(14) 0.0380(6) Uani 1 1 d . . . . .
C13 C -0.3865(7) 0.5885(4) 0.19387(14) 0.0345(6) Uani 1 1 d . . . . .
C14 C -0.6138(9) 0.6652(5) 0.08901(15) 0.0439(7) Uani 1 1 d . . . . .
C15 C -0.3280(8) 0.6725(4) 0.25547(14) 0.0343(6) Uani 1 1 d . . . . .
C16 C -0.7779(9) 0.8121(5) 0.05067(14) 0.0416(7) Uani 1 1 d . . . . .
H9 H -0.160(11) 0.782(8) 0.376(2) 0.063(12) Uiso 1 1 d . . . . .
H15 H -0.391(9) 0.798(7) 0.2665(18) 0.045(10) Uiso 1 1 d . . . . .
H1 H 0.173(8) 0.091(6) 0.3099(16) 0.036(8) Uiso 1 1 d . . . . .
H11 H -0.330(9) 0.317(6) 0.1339(18) 0.040(9) Uiso 1 1 d . . . . .
H8 H -0.051(8) 0.122(5) 0.2033(15) 0.031(8) Uiso 1 1 d . . . . .
H7 H 0.091(10) 0.587(7) 0.448(2) 0.057(11) Uiso 1 1 d . . . . .
H12 H -0.610(10) 0.856(7) 0.167(2) 0.054(11) Uiso 1 1 d . . . . .
H14 H -0.548(11) 0.529(7) 0.067(2) 0.055(11) Uiso 1 1 d . . . . .
H2 H -0.926(19) 0.848(13) -0.030(4) 0.13(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.905(3) . ?
C1 C6 1.366(4) . ?
C1 C10 1.414(4) . ?
O2 C16 1.262(4) . ?
O4 C16 1.271(4) . ?
C5 C9 1.412(4) . ?
C5 C10 1.423(4) . ?
C5 C15 1.405(4) . ?
C6 C7 1.404(4) . ?
C7 C9 1.360(4) . ?
C8 C10 1.419(4) . ?
C8 C11 1.357(4) . ?
C11 C13 1.426(4) . ?
C12 C13 1.459(4) . ?
C12 C14 1.326(5) . ?
C13 C15 1.370(4) . ?
C14 C16 1.465(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C10 119.1(3) . . ?
C9 C5 C10 118.7(3) . . ?
C15 C5 C9 122.8(3) . . ?
C15 C5 C10 118.5(3) . . ?
C1 C6 Br1 119.3(2) . . ?
C1 C6 C7 122.6(3) . . ?
C7 C6 Br1 118.1(2) . . ?
C9 C7 C6 118.7(3) . . ?
C11 C8 C10 121.3(3) . . ?
C7 C9 C5 121.6(3) . . ?
C1 C10 C5 119.3(2) . . ?
C1 C10 C8 122.2(3) . . ?
C8 C10 C5 118.5(3) . . ?
C8 C11 C13 120.7(3) . . ?
C14 C12 C13 127.8(3) . . ?
C11 C13 C12 122.0(3) . . ?
C15 C13 C11 118.4(3) . . ?
C15 C13 C12 119.6(3) . . ?
C12 C14 C16 121.7(3) . . ?
C13 C15 C5 122.5(3) . . ?
O2 C16 O4 122.4(3) . . ?
O2 C16 C14 118.2(3) . . ?
O4 C16 C14 119.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1ClNaAA
_audit_block_doi                 10.5517/ccdc.csd.cc23dqy6
_database_code_depnum_ccdc_archive 'CCDC 1948658'
loop_
_audit_author_name
_audit_author_address
'Jiaxi Liu'
;Jilin University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;
_audit_creation_date             2019-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Cl O2'
_chemical_formula_sum            'C13 H9 Cl O2'
_chemical_formula_weight         232.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.7709(7)
_cell_length_b                   7.9900(14)
_cell_length_c                   17.205(3)
_cell_angle_alpha                91.451(7)
_cell_angle_beta                 90.871(7)
_cell_angle_gamma                91.865(7)
_cell_volume                     517.87(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4295
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.619
_cell_measurement_theta_min      3.438
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10200
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.388
_diffrn_reflns_theta_min         3.437
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1859
_reflns_number_total             3229
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.835
_refine_diff_density_min         -1.040
_refine_diff_density_rms         0.183
_refine_ls_extinction_coef       0.17(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1782
_refine_ls_R_factor_gt           0.1117
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1954P)²+0.7990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2969
_refine_ls_wR_factor_ref         0.3717
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All O(H) groups
2.a Everything fixed:
 H1
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.4810(3) 0.70076(14) 0.84349(7) 0.0365(5) Uani 1 1 d . . . . .
O1 O 0.2134(11) 0.9467(4) 0.5863(2) 0.0421(9) Uani 1 1 d . . . . .
H1 H 0.2257 1.0356 0.5503 0.051 Uiso 1 1 d . . . . .
O2 O -0.0293(11) 0.7838(5) 0.4896(2) 0.0401(9) Uani 1 1 d . . . . .
C1 C 0.1345(14) 0.8036(6) 0.5549(3) 0.0357(11) Uani 1 1 d . . . . .
C2 C 0.2396(14) 0.6504(6) 0.5958(3) 0.0357(11) Uani 1 1 d . . . . .
H2 H 0.187(13) 0.549(7) 0.562(3) 0.023(12) Uiso 1 1 d . . . . .
C3 C 0.3822(14) 0.6566(6) 0.6669(3) 0.0352(11) Uani 1 1 d . . . . .
H3 H 0.404(16) 0.758(8) 0.697(4) 0.039(15) Uiso 1 1 d . . . . .
C4 C 0.5053(14) 0.5112(6) 0.7100(3) 0.0336(10) Uani 1 1 d . . . . .
C5 C 0.5779(14) 0.3582(6) 0.6683(3) 0.0355(11) Uani 1 1 d . . . . .
H5 H 0.533(17) 0.348(8) 0.618(4) 0.042(17) Uiso 1 1 d . . . . .
C6 C 0.7166(14) 0.2234(6) 0.7053(3) 0.0359(11) Uani 1 1 d . . . . .
H6 H 0.799(14) 0.127(7) 0.675(3) 0.027(13) Uiso 1 1 d . . . . .
C7 C 0.7933(13) 0.2331(6) 0.7865(3) 0.0342(10) Uani 1 1 d . . . . .
C8 C 0.9475(14) 0.0950(6) 0.8248(3) 0.0368(11) Uani 1 1 d . . . . .
H8 H 1.017(16) -0.017(8) 0.794(4) 0.037(15) Uiso 1 1 d . . . . .
C9 C 1.0167(14) 0.1049(6) 0.9042(3) 0.0369(11) Uani 1 1 d . . . . .
H9 H 1.114(17) 0.001(8) 0.930(4) 0.045(17) Uiso 1 1 d . . . . .
C10 C 0.9358(15) 0.2498(7) 0.9481(3) 0.0392(11) Uani 1 1 d . . . . .
C11 C 0.7877(14) 0.3856(6) 0.9123(3) 0.0359(11) Uani 1 1 d . . . . .
H11 H 0.731(14) 0.481(7) 0.942(3) 0.023(12) Uiso 1 1 d . . . . .
C12 C 0.7158(13) 0.3803(5) 0.8309(3) 0.0324(10) Uani 1 1 d . . . . .
C13 C 0.5730(13) 0.5187(6) 0.7893(3) 0.0327(10) Uani 1 1 d . . . . .
H10 H 0.981(17) 0.261(9) 1.012(4) 0.046(17) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C13 1.756(5) . ?
O1 H1 0.9543 . ?
O1 C1 1.276(6) . ?
O2 C1 1.277(6) . ?
C1 C2 1.489(7) . ?
C2 H2 1.00(5) . ?
C2 C3 1.327(8) . ?
C3 H3 0.95(6) . ?
C3 C4 1.478(7) . ?
C4 C5 1.438(7) . ?
C4 C13 1.384(7) . ?
C5 H5 0.88(7) . ?
C5 C6 1.378(7) . ?
C6 H6 0.99(6) . ?
C6 C7 1.422(8) . ?
C7 C8 1.434(7) . ?
C7 C12 1.427(7) . ?
C8 H8 1.07(6) . ?
C8 C9 1.385(8) . ?
C9 H9 1.02(7) . ?
C9 C10 1.411(8) . ?
C10 C11 1.390(7) . ?
C10 H10 1.10(7) . ?
C11 H11 0.94(5) . ?
C11 C12 1.421(7) . ?
C12 C13 1.447(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 113.9 . . ?
O1 C1 O2 123.6(5) . . ?
O1 C1 C2 118.7(5) . . ?
O2 C1 C2 117.7(5) . . ?
C1 C2 H2 110(3) . . ?
C3 C2 C1 122.4(5) . . ?
C3 C2 H2 127(3) . . ?
C2 C3 H3 122(4) . . ?
C2 C3 C4 125.5(5) . . ?
C4 C3 H3 112(4) . . ?
C5 C4 C3 119.6(5) . . ?
C13 C4 C3 122.4(5) . . ?
C13 C4 C5 117.9(5) . . ?
C4 C5 H5 121(4) . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 H5 118(4) . . ?
C5 C6 H6 120(3) . . ?
C5 C6 C7 120.3(5) . . ?
C7 C6 H6 119(3) . . ?
C6 C7 C8 120.5(5) . . ?
C6 C7 C12 120.3(4) . . ?
C12 C7 C8 119.2(5) . . ?
C7 C8 H8 122(3) . . ?
C9 C8 C7 120.1(5) . . ?
C9 C8 H8 118(3) . . ?
C8 C9 H9 117(4) . . ?
C8 C9 C10 120.7(5) . . ?
C10 C9 H9 122(4) . . ?
C9 C10 H10 123(4) . . ?
C11 C10 C9 120.4(5) . . ?
C11 C10 H10 117(4) . . ?
C10 C11 H11 120(3) . . ?
C10 C11 C12 120.4(5) . . ?
C12 C11 H11 119(3) . . ?
C7 C12 C13 117.2(4) . . ?
C11 C12 C7 119.3(4) . . ?
C11 C12 C13 123.5(5) . . ?
C4 C13 Cl1 119.9(4) . . ?
C4 C13 C12 122.7(5) . . ?
C12 C13 Cl1 117.4(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1BrNaAA
_audit_block_doi                 10.5517/ccdc.csd.cc23dnt0
_database_code_depnum_ccdc_archive 'CCDC 1948592'
loop_
_audit_author_name
_audit_author_address
'Jiaxi Liu'
;Jilin University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Br O2'
_chemical_formula_sum            'C13 H9 Br O2'
_chemical_formula_weight         277.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8948(4)
_cell_length_b                   8.1149(8)
_cell_length_c                   17.1274(16)
_cell_angle_alpha                90.194(3)
_cell_angle_beta                 91.725(4)
_cell_angle_gamma                92.396(4)
_cell_volume                     540.60(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8167
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.174
_cell_measurement_theta_min      2.785
_shelx_estimated_absorpt_T_max   0.660
_shelx_estimated_absorpt_T_min   0.601
_exptl_absorpt_coefficient_mu    3.781
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11440
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.245
_diffrn_reflns_theta_min         2.775
_diffrn_ambient_temperature      293.76
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1929
_reflns_number_total             2164
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0264
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+0.2656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0633
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Everything fixed:
 H1
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.52082(7) 0.29289(3) 0.15373(2) 0.04117(10) Uani 1 1 d . . . . .
O1 O 1.0187(6) 0.2130(2) 0.51149(10) 0.0570(5) Uani 1 1 d . . . . .
H1 H 1.0628 0.1111 0.5337 0.062 Uani 1 1 d . . . . .
O2 O 0.8021(6) 0.0571(2) 0.41348(11) 0.0617(6) Uani 1 1 d . . . . .
C1 C 0.4209(5) 0.4844(3) 0.21252(12) 0.0283(4) Uani 1 1 d . . . . .
C2 C 0.2783(5) 0.6191(3) 0.17133(12) 0.0288(5) Uani 1 1 d . . . . .
C7 C 0.2048(6) 0.7613(3) 0.21558(13) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.2017(6) 0.6188(3) 0.08969(13) 0.0360(5) Uani 1 1 d . . . . .
C8 C 0.2842(7) 0.7654(3) 0.29671(14) 0.0399(6) Uani 1 1 d . . . . .
C10 C 0.4925(6) 0.4873(3) 0.29192(13) 0.0317(5) Uani 1 1 d . . . . .
C6 C 0.0501(7) 0.8947(3) 0.17748(15) 0.0399(6) Uani 1 1 d . . . . .
C9 C 0.4233(7) 0.6347(3) 0.33304(14) 0.0393(6) Uani 1 1 d . . . . .
C4 C 0.0541(7) 0.7514(3) 0.05554(15) 0.0425(6) Uani 1 1 d . . . . .
C5 C -0.0245(7) 0.8900(3) 0.09933(16) 0.0440(6) Uani 1 1 d . . . . .
C11 C 0.6195(7) 0.3447(3) 0.33439(14) 0.0374(5) Uani 1 1 d . . . . .
C12 C 0.7576(7) 0.3462(3) 0.40611(15) 0.0427(6) Uani 1 1 d . . . . .
C13 C 0.8653(7) 0.1960(3) 0.44540(13) 0.0402(6) Uani 1 1 d . . . . .
H3 H 0.252(7) 0.522(3) 0.0626(16) 0.041(7) Uiso 1 1 d . . . . .
H6 H 0.005(7) 0.982(4) 0.2059(16) 0.042(7) Uiso 1 1 d . . . . .
H5 H -0.136(8) 0.977(4) 0.0729(18) 0.056(8) Uiso 1 1 d . . . . .
H9 H 0.468(7) 0.640(3) 0.3842(17) 0.046(8) Uiso 1 1 d . . . . .
H8 H 0.242(7) 0.861(4) 0.3249(17) 0.049(8) Uiso 1 1 d . . . . .
H11 H 0.585(7) 0.250(4) 0.3093(17) 0.049(8) Uiso 1 1 d . . . . .
H4 H -0.002(8) 0.753(4) 0.0023(19) 0.055(8) Uiso 1 1 d . . . . .
H12 H 0.805(9) 0.449(4) 0.437(2) 0.070(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.909(2) . ?
O1 H1 0.9315 . ?
O1 C13 1.268(3) . ?
O2 C13 1.263(3) . ?
C1 C2 1.426(3) . ?
C1 C10 1.380(3) . ?
C2 C7 1.422(3) . ?
C2 C3 1.421(3) . ?
C7 C8 1.415(3) . ?
C7 C6 1.413(3) . ?
C3 C4 1.366(3) . ?
C3 H3 0.94(3) . ?
C8 C9 1.356(4) . ?
C8 H8 0.93(3) . ?
C10 C9 1.425(3) . ?
C10 C11 1.464(3) . ?
C6 C5 1.361(4) . ?
C6 H6 0.88(3) . ?
C9 H9 0.89(3) . ?
C4 C5 1.399(4) . ?
C4 H4 0.93(3) . ?
C5 H5 0.95(3) . ?
C11 C12 1.326(4) . ?
C11 H11 0.88(3) . ?
C12 C13 1.465(3) . ?
C12 H12 1.00(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 H1 111.3 . . ?
C2 C1 Br1 117.74(15) . . ?
C10 C1 Br1 119.08(16) . . ?
C10 C1 C2 123.18(19) . . ?
C7 C2 C1 117.36(19) . . ?
C3 C2 C1 124.2(2) . . ?
C3 C2 C7 118.4(2) . . ?
C8 C7 C2 119.4(2) . . ?
C6 C7 C2 119.1(2) . . ?
C6 C7 C8 121.5(2) . . ?
C2 C3 H3 115.8(17) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 124.0(17) . . ?
C7 C8 H8 118.7(17) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 120.4(17) . . ?
C1 C10 C9 117.1(2) . . ?
C1 C10 C11 122.7(2) . . ?
C9 C10 C11 120.1(2) . . ?
C7 C6 H6 117.8(18) . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 121.0(18) . . ?
C8 C9 C10 121.9(2) . . ?
C8 C9 H9 119.3(18) . . ?
C10 C9 H9 118.7(18) . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4 121.5(19) . . ?
C5 C4 H4 117.1(19) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 122.4(18) . . ?
C4 C5 H5 117.8(18) . . ?
C10 C11 H11 114.0(19) . . ?
C12 C11 C10 126.2(2) . . ?
C12 C11 H11 119.7(19) . . ?
C11 C12 C13 122.5(2) . . ?
C11 C12 H12 123(2) . . ?
C13 C12 H12 114(2) . . ?
O1 C13 C12 117.2(2) . . ?
O2 C13 O1 122.9(2) . . ?
O2 C13 C12 119.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1INaAA
_audit_block_doi                 10.5517/ccdc.csd.cc23dnw2
_database_code_depnum_ccdc_archive 'CCDC 1948594'
loop_
_audit_author_name
_audit_author_address
'Jiaxi Liu'
;Jilin University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;
_audit_creation_date             2019-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 I O2'
_chemical_formula_sum            'C13 H9 I O2'
_chemical_formula_weight         324.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8142(2)
_cell_length_b                   8.2211(4)
_cell_length_c                   14.3363(7)
_cell_angle_alpha                102.141(2)
_cell_angle_beta                 91.410(2)
_cell_angle_gamma                93.280(2)
_cell_volume                     553.41(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6130
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.08
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.873
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.945
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7300
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.104
_diffrn_reflns_theta_min         2.909
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2537
_reflns_number_total             2953
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0233P)²+0.2836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0633
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.55755(4) 0.56680(3) 0.83550(2) 0.02823(8) Uani 1 1 d . . . . .
O1 O 1.3088(5) 0.3008(3) 0.46192(15) 0.0257(5) Uani 1 1 d . . . . .
O2 O 1.2664(4) 0.5177(2) 0.58417(15) 0.0220(4) Uani 1 1 d . . . . .
C1 C -0.1402(6) 0.0263(4) 0.8884(2) 0.0296(7) Uani 1 1 d . . . . .
H1A H -0.2772 -0.0383 0.9138 0.035 Uiso 1 1 calc R . . . .
C2 C -0.0103(6) -0.0416(4) 0.8062(2) 0.0256(7) Uani 1 1 d . . . . .
H2 H -0.0583 -0.1540 0.7751 0.031 Uiso 1 1 calc R . . . .
C3 C 0.1941(6) 0.0531(4) 0.7669(2) 0.0213(6) Uani 1 1 d . . . . .
C4 C 0.2638(6) 0.2209(4) 0.8135(2) 0.0183(6) Uani 1 1 d . . . . .
C5 C 0.4708(6) 0.3128(3) 0.7716(2) 0.0179(5) Uani 1 1 d . . . . .
C6 C 0.6077(6) 0.2403(4) 0.6905(2) 0.0183(6) Uani 1 1 d . . . . .
C7 C 0.8307(5) 0.3308(4) 0.6506(2) 0.0192(6) Uani 1 1 d . . . . .
H7 H 0.8866 0.4401 0.6850 0.023 Uiso 1 1 calc R . . . .
C8 C 0.9622(6) 0.2746(4) 0.5706(2) 0.0209(6) Uani 1 1 d . . . . .
H8 H 0.9077 0.1677 0.5327 0.025 Uiso 1 1 calc R . . . .
C9 C 1.1905(5) 0.3756(4) 0.5405(2) 0.0195(6) Uani 1 1 d . . . . .
C10 C -0.0681(6) 0.1920(4) 0.9344(2) 0.0268(7) Uani 1 1 d . . . . .
H10 H -0.1560 0.2387 0.9916 0.032 Uiso 1 1 calc R . . . .
C11 C 0.1265(6) 0.2874(4) 0.8983(2) 0.0234(6) Uani 1 1 d . . . . .
H11 H 0.1703 0.3996 0.9305 0.028 Uiso 1 1 calc R . . . .
C12 C 0.3290(6) -0.0187(4) 0.6833(2) 0.0231(6) Uani 1 1 d . . . . .
H12 H 0.2801 -0.1309 0.6521 0.028 Uiso 1 1 calc R . . . .
C13 C 0.5295(6) 0.0720(4) 0.6470(2) 0.0209(6) Uani 1 1 d . . . . .
H13 H 0.6191 0.0210 0.5911 0.025 Uiso 1 1 calc R . . . .
H1 H 1.459(9) 0.358(6) 0.448(3) 0.060(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C5 2.109(3) . ?
O1 C9 1.323(3) . ?
O1 H1 0.89(5) . ?
O2 C9 1.234(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.376(4) . ?
C1 C10 1.403(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.420(4) . ?
C3 C4 1.418(4) . ?
C3 C12 1.411(4) . ?
C4 C5 1.435(4) . ?
C4 C11 1.420(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.467(4) . ?
C6 C13 1.418(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.332(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.468(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.367(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.365(4) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 H1 113(3) . . ?
C2 C1 H1A 120.4 . . ?
C2 C1 C10 119.3(3) . . ?
C10 C1 H1A 120.4 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 119.1(3) . . ?
C12 C3 C2 120.7(3) . . ?
C12 C3 C4 120.2(3) . . ?
C3 C4 C5 117.5(2) . . ?
C3 C4 C11 118.4(3) . . ?
C11 C4 C5 124.1(3) . . ?
C4 C5 I1 117.74(19) . . ?
C6 C5 I1 120.2(2) . . ?
C6 C5 C4 122.0(3) . . ?
C5 C6 C7 122.2(3) . . ?
C5 C6 C13 118.0(2) . . ?
C13 C6 C7 119.8(2) . . ?
C6 C7 H7 116.9 . . ?
C8 C7 C6 126.3(3) . . ?
C8 C7 H7 116.9 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
O1 C9 C8 114.0(3) . . ?
O2 C9 O1 122.7(3) . . ?
O2 C9 C8 123.3(3) . . ?
C1 C10 H10 119.4 . . ?
C11 C10 C1 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C4 C11 H11 119.6 . . ?
C10 C11 C4 120.9(3) . . ?
C10 C11 H11 119.6 . . ?
C3 C12 H12 119.8 . . ?
C13 C12 C3 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C6 C13 H13 119.1 . . ?
C12 C13 C6 121.9(3) . . ?
C12 C13 H13 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C5 C6 C7 4.9(4) . . . . ?
I1 C5 C6 C13 -176.2(2) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C1 C2 C3 C12 179.0(3) . . . . ?
C1 C10 C11 C4 -0.6(5) . . . . ?
C2 C1 C10 C11 0.7(5) . . . . ?
C2 C3 C4 C5 -179.9(3) . . . . ?
C2 C3 C4 C11 0.3(4) . . . . ?
C2 C3 C12 C13 -178.6(3) . . . . ?
C3 C4 C5 I1 176.2(2) . . . . ?
C3 C4 C5 C6 -2.5(4) . . . . ?
C3 C4 C11 C10 0.1(4) . . . . ?
C3 C12 C13 C6 -0.6(5) . . . . ?
C4 C3 C12 C13 0.6(5) . . . . ?
C4 C5 C6 C7 -176.4(3) . . . . ?
C4 C5 C6 C13 2.4(4) . . . . ?
C5 C4 C11 C10 -179.7(3) . . . . ?
C5 C6 C7 C8 -176.1(3) . . . . ?
C5 C6 C13 C12 -0.9(4) . . . . ?
C6 C7 C8 C9 -177.5(3) . . . . ?
C7 C6 C13 C12 178.0(3) . . . . ?
C7 C8 C9 O1 177.3(3) . . . . ?
C7 C8 C9 O2 -2.6(5) . . . . ?
C10 C1 C2 C3 -0.3(5) . . . . ?
C11 C4 C5 I1 -4.0(4) . . . . ?
C11 C4 C5 C6 177.3(3) . . . . ?
C12 C3 C4 C5 0.9(4) . . . . ?
C12 C3 C4 C11 -178.9(3) . . . . ?
C13 C6 C7 C8 5.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_D-1FNaAA
_audit_block_doi                 10.5517/ccdc.csd.cc23mgt1
_database_code_depnum_ccdc_archive 'CCDC 1955133'
loop_
_audit_author_name
_audit_author_address
'Jiaxi Liu'
;Jilin University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;
_audit_creation_date             2019-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H18 F2 O4, C3 H6 O'
_chemical_formula_sum            'C29 H24 F2 O5'
_chemical_formula_weight         490.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4331(7)
_cell_length_b                   21.337(2)
_cell_length_c                   15.4508(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.686(5)
_cell_angle_gamma                90
_cell_volume                     2422.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7219
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.32
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1749
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            75776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.488
_diffrn_reflns_theta_min         2.889
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3525
_reflns_number_total             6668
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6668
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1494
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+1.6903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.21798(16) 0.76201(6) 0.66010(9) 0.0288(3) Uani 1 1 d . . . . .
F002 F 0.20801(17) 0.77166(6) 0.44872(10) 0.0319(3) Uani 1 1 d . . . . .
O003 O 0.2121(2) 0.49379(7) 0.46474(11) 0.0251(4) Uani 1 1 d . . . . .
O004 O 0.5574(2) 0.56243(8) 0.75151(11) 0.0294(4) Uani 1 1 d . . . . .
O005 O 0.0937(2) 0.56499(7) 0.54690(12) 0.0303(4) Uani 1 1 d . . . . .
O006 O 0.4126(2) 0.49328(7) 0.65604(11) 0.0290(4) Uani 1 1 d . . . . .
O007 O 0.4905(3) 0.48009(9) 0.87536(12) 0.0424(5) Uani 1 1 d . . . . .
C008 C 0.4994(3) 0.71386(10) 0.65291(15) 0.0196(5) Uani 1 1 d . . . . .
C009 C 0.4491(3) 0.69956(10) 0.45942(15) 0.0212(5) Uani 1 1 d . . . . .
C00A C 0.6747(3) 0.82418(10) 0.72613(15) 0.0223(5) Uani 1 1 d . . . . .
C00B C 0.4037(3) 0.76474(10) 0.67501(15) 0.0211(5) Uani 1 1 d . . . . .
C00C C 0.4958(3) 0.59406(10) 0.60348(15) 0.0208(5) Uani 1 1 d . . . . .
C00D C 0.2200(3) 0.54565(10) 0.50818(15) 0.0224(5) Uani 1 1 d . . . . .
C00E C 0.4815(3) 0.82074(10) 0.71194(15) 0.0213(5) Uani 1 1 d . . . . .
C00F C 0.4825(3) 0.54402(10) 0.67085(16) 0.0221(5) Uani 1 1 d . . . . .
C00G C 0.3978(3) 0.65754(10) 0.61200(15) 0.0208(5) Uani 1 1 d . . . . .
C00H C 0.3794(3) 0.75687(11) 0.43386(15) 0.0233(5) Uani 1 1 d . . . . .
C00I C 0.3882(3) 0.58502(10) 0.51007(16) 0.0224(5) Uani 1 1 d . . . . .
C00J C 0.3398(3) 0.65630(10) 0.50875(15) 0.0207(5) Uani 1 1 d . . . . .
C00K C 0.6918(3) 0.71897(11) 0.66824(16) 0.0236(5) Uani 1 1 d . . . . .
C00L C 0.6499(3) 0.78905(11) 0.37591(15) 0.0250(5) Uani 1 1 d . . . . .
C00M C 0.7761(3) 0.77202(11) 0.70326(16) 0.0255(5) Uani 1 1 d . . . . .
C00N C 0.4703(3) 0.80349(11) 0.39153(15) 0.0239(5) Uani 1 1 d . . . . .
C00O C 0.6274(3) 0.68636(11) 0.44181(16) 0.0255(5) Uani 1 1 d . . . . .
C00P C 0.3769(3) 0.87214(11) 0.73572(17) 0.0272(5) Uani 1 1 d . . . . .
C00Q C 0.7574(3) 0.88023(11) 0.76336(16) 0.0262(5) Uani 1 1 d . . . . .
C00R C 0.7248(3) 0.72971(12) 0.40198(17) 0.0281(5) Uani 1 1 d . . . . .
C00S C 0.6549(3) 0.92920(11) 0.78482(17) 0.0290(6) Uani 1 1 d . . . . .
C00T C 0.7432(4) 0.83524(12) 0.33289(16) 0.0294(6) Uani 1 1 d . . . . .
C00U C 0.4624(4) 0.92511(11) 0.77154(17) 0.0307(6) Uani 1 1 d . . . . .
C00V C 0.3889(4) 0.86150(11) 0.36388(17) 0.0301(6) Uani 1 1 d . . . . .
C00W C 0.6617(4) 0.89076(12) 0.30684(17) 0.0317(6) Uani 1 1 d . . . . .
C00X C 0.4842(4) 0.90413(12) 0.32160(17) 0.0327(6) Uani 1 1 d . . . . .
C00Y C 0.5759(4) 0.44320(13) 0.92643(17) 0.0366(6) Uani 1 1 d . . . . .
C00Z C 0.4788(6) 0.39181(18) 0.9667(2) 0.0553(9) Uani 1 1 d . . . . .
C010 C 0.7759(5) 0.4478(2) 0.9522(2) 0.0540(9) Uani 1 1 d . . . . .
H00C H 0.628(3) 0.5995(10) 0.5997(15) 0.019(6) Uiso 1 1 d . . . . .
H00J H 0.213(3) 0.6650(9) 0.4895(14) 0.013(5) Uiso 1 1 d . . . . .
H00X H 0.424(3) 0.9462(12) 0.3023(18) 0.039(7) Uiso 1 1 d . . . . .
H00M H 0.912(4) 0.7774(12) 0.7145(18) 0.041(8) Uiso 1 1 d . . . . .
H00W H 0.733(3) 0.9234(10) 0.2789(15) 0.021(6) Uiso 1 1 d . . . . .
H00R H 0.850(4) 0.7197(11) 0.3901(17) 0.037(7) Uiso 1 1 d . . . . .
H00I H 0.462(3) 0.5686(10) 0.4644(15) 0.019(6) Uiso 1 1 d . . . . .
H00K H 0.760(3) 0.6820(11) 0.6534(16) 0.029(7) Uiso 1 1 d . . . . .
H00Q H 0.892(4) 0.8831(12) 0.7726(17) 0.040(8) Uiso 1 1 d . . . . .
H00T H 0.866(4) 0.8250(12) 0.3236(17) 0.039(8) Uiso 1 1 d . . . . .
H00U H 0.392(3) 0.9608(12) 0.7888(16) 0.031(7) Uiso 1 1 d . . . . .
H00G H 0.289(3) 0.6511(10) 0.6402(16) 0.026(6) Uiso 1 1 d . . . . .
H00P H 0.240(4) 0.8691(12) 0.7257(17) 0.040(8) Uiso 1 1 d . . . . .
H00S H 0.713(3) 0.9687(12) 0.8117(17) 0.034(7) Uiso 1 1 d . . . . .
H00V H 0.258(4) 0.8697(12) 0.3716(17) 0.041(8) Uiso 1 1 d . . . . .
H00O H 0.682(3) 0.6453(11) 0.4586(16) 0.029(7) Uiso 1 1 d . . . . .
H01A H 0.829(5) 0.4824(18) 0.921(3) 0.087(13) Uiso 1 1 d . . . . .
H00A H 0.528(5) 0.3539(17) 0.953(3) 0.080(13) Uiso 1 1 d . . . . .
H01B H 0.805(5) 0.4562(16) 1.016(3) 0.081(12) Uiso 1 1 d . . . . .
H004 H 0.542(5) 0.5271(17) 0.799(3) 0.090(12) Uiso 1 1 d . . . . .
H00B H 0.337(5) 0.3953(16) 0.950(2) 0.085(12) Uiso 1 1 d . . . . .
H003 H 0.063(6) 0.467(2) 0.460(3) 0.138(17) Uiso 1 1 d . . . . .
H00D H 0.509(5) 0.3938(17) 1.035(3) 0.091(13) Uiso 1 1 d . . . . .
H01C H 0.829(6) 0.406(2) 0.949(3) 0.108(16) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00B 1.366(2) . ?
F002 C00H 1.365(2) . ?
O003 C00D 1.291(3) . ?
O003 H003 1.24(5) . ?
O004 C00F 1.345(3) . ?
O004 H004 1.07(4) . ?
O005 C00D 1.257(3) . ?
O006 C00F 1.208(3) . ?
O007 C00Y 1.222(3) . ?
C008 C00B 1.369(3) . ?
C008 C00G 1.506(3) . ?
C008 C00K 1.418(3) . ?
C009 C00H 1.363(3) . ?
C009 C00J 1.510(3) . ?
C009 C00O 1.421(3) . ?
C00A C00E 1.422(3) . ?
C00A C00M 1.418(3) . ?
C00A C00Q 1.425(3) . ?
C00B C00E 1.410(3) . ?
C00C C00F 1.505(3) . ?
C00C C00G 1.553(3) . ?
C00C C00I 1.553(3) . ?
C00C H00C 1.00(2) . ?
C00D C00I 1.503(3) . ?
C00E C00P 1.424(3) . ?
C00G C00J 1.589(3) . ?
C00G H00G 0.98(2) . ?
C00H C00N 1.417(3) . ?
C00I C00J 1.562(3) . ?
C00I H00I 1.02(2) . ?
C00J H00J 0.96(2) . ?
C00K C00M 1.366(3) . ?
C00K H00K 0.98(2) . ?
C00L C00N 1.426(3) . ?
C00L C00R 1.417(3) . ?
C00L C00T 1.426(3) . ?
C00M H00M 1.01(3) . ?
C00N C00V 1.415(3) . ?
C00O C00R 1.376(3) . ?
C00O H00O 0.98(2) . ?
C00P C00U 1.372(3) . ?
C00P H00P 1.01(3) . ?
C00Q C00S 1.363(3) . ?
C00Q H00Q 0.99(3) . ?
C00R H00R 1.00(3) . ?
C00S C00U 1.417(4) . ?
C00S H00S 1.01(3) . ?
C00T C00W 1.363(4) . ?
C00T H00T 0.97(3) . ?
C00U H00U 0.98(2) . ?
C00V C00X 1.377(3) . ?
C00V H00V 1.01(3) . ?
C00W C00X 1.402(4) . ?
C00W H00W 1.01(2) . ?
C00X H00X 1.02(3) . ?
C00Y C00Z 1.499(4) . ?
C00Y C010 1.483(4) . ?
C00Z H00A 0.93(4) . ?
C00Z H00B 1.05(4) . ?
C00Z H00D 1.05(4) . ?
C010 H01A 1.00(4) . ?
C010 H01B 0.99(4) . ?
C010 H01C 0.97(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00D O003 H003 113.2(19) . . ?
C00F O004 H004 111(2) . . ?
C00B C008 C00G 119.41(19) . . ?
C00B C008 C00K 116.5(2) . . ?
C00K C008 C00G 124.06(19) . . ?
C00H C009 C00J 119.0(2) . . ?
C00H C009 C00O 116.6(2) . . ?
C00O C009 C00J 124.3(2) . . ?
C00E C00A C00Q 118.0(2) . . ?
C00M C00A C00E 118.9(2) . . ?
C00M C00A C00Q 123.1(2) . . ?
F001 C00B C008 118.29(19) . . ?
F001 C00B C00E 116.54(19) . . ?
C008 C00B C00E 125.2(2) . . ?
C00F C00C C00G 118.66(19) . . ?
C00F C00C C00I 118.45(19) . . ?
C00F C00C H00C 106.9(13) . . ?
C00G C00C H00C 112.3(12) . . ?
C00I C00C C00G 90.27(17) . . ?
C00I C00C H00C 109.5(13) . . ?
O003 C00D C00I 117.47(19) . . ?
O005 C00D O003 123.4(2) . . ?
O005 C00D C00I 119.1(2) . . ?
C00A C00E C00P 119.9(2) . . ?
C00B C00E C00A 116.71(19) . . ?
C00B C00E C00P 123.4(2) . . ?
O004 C00F C00C 111.88(19) . . ?
O006 C00F O004 122.9(2) . . ?
O006 C00F C00C 125.2(2) . . ?
C008 C00G C00C 121.32(19) . . ?
C008 C00G C00J 118.52(19) . . ?
C008 C00G H00G 108.5(13) . . ?
C00C C00G C00J 87.71(16) . . ?
C00C C00G H00G 110.0(13) . . ?
C00J C00G H00G 109.1(14) . . ?
F002 C00H C00N 115.94(19) . . ?
C009 C00H F002 118.83(19) . . ?
C009 C00H C00N 125.2(2) . . ?
C00C C00I C00J 88.66(17) . . ?
C00C C00I H00I 115.5(13) . . ?
C00D C00I C00C 113.43(19) . . ?
C00D C00I C00J 110.76(18) . . ?
C00D C00I H00I 109.1(12) . . ?
C00J C00I H00I 118.2(12) . . ?
C009 C00J C00G 114.29(18) . . ?
C009 C00J C00I 117.46(19) . . ?
C009 C00J H00J 107.6(12) . . ?
C00G C00J H00J 114.3(13) . . ?
C00I C00J C00G 88.63(16) . . ?
C00I C00J H00J 113.9(12) . . ?
C008 C00K H00K 116.2(14) . . ?
C00M C00K C008 121.4(2) . . ?
C00M C00K H00K 122.4(14) . . ?
C00N C00L C00T 117.6(2) . . ?
C00R C00L C00N 118.9(2) . . ?
C00R C00L C00T 123.5(2) . . ?
C00A C00M H00M 115.1(15) . . ?
C00K C00M C00A 121.3(2) . . ?
C00K C00M H00M 123.6(15) . . ?
C00H C00N C00L 116.8(2) . . ?
C00V C00N C00H 122.8(2) . . ?
C00V C00N C00L 120.4(2) . . ?
C009 C00O H00O 119.2(14) . . ?
C00R C00O C009 121.4(2) . . ?
C00R C00O H00O 119.3(14) . . ?
C00E C00P H00P 119.2(15) . . ?
C00U C00P C00E 120.1(2) . . ?
C00U C00P H00P 120.7(15) . . ?
C00A C00Q H00Q 118.3(15) . . ?
C00S C00Q C00A 121.2(2) . . ?
C00S C00Q H00Q 120.5(15) . . ?
C00L C00R H00R 118.4(14) . . ?
C00O C00R C00L 121.1(2) . . ?
C00O C00R H00R 120.5(14) . . ?
C00Q C00S C00U 120.4(2) . . ?
C00Q C00S H00S 121.3(14) . . ?
C00U C00S H00S 118.2(14) . . ?
C00L C00T H00T 116.7(15) . . ?
C00W C00T C00L 120.8(2) . . ?
C00W C00T H00T 122.5(15) . . ?
C00P C00U C00S 120.3(2) . . ?
C00P C00U H00U 121.1(15) . . ?
C00S C00U H00U 118.5(14) . . ?
C00N C00V H00V 119.3(15) . . ?
C00X C00V C00N 119.6(2) . . ?
C00X C00V H00V 120.9(15) . . ?
C00T C00W C00X 121.1(2) . . ?
C00T C00W H00W 119.2(13) . . ?
C00X C00W H00W 119.6(13) . . ?
C00V C00X C00W 120.5(2) . . ?
C00V C00X H00X 119.0(15) . . ?
C00W C00X H00X 120.5(15) . . ?
O007 C00Y C00Z 120.3(3) . . ?
O007 C00Y C010 122.1(3) . . ?
C010 C00Y C00Z 117.6(3) . . ?
C00Y C00Z H00A 108(2) . . ?
C00Y C00Z H00B 112(2) . . ?
C00Y C00Z H00D 110(2) . . ?
H00A C00Z H00B 115(3) . . ?
H00A C00Z H00D 103(3) . . ?
H00B C00Z H00D 107(3) . . ?
C00Y C010 H01A 112(2) . . ?
C00Y C010 H01B 110(2) . . ?
C00Y C010 H01C 109(3) . . ?
H01A C010 H01B 108(3) . . ?
H01A C010 H01C 117(3) . . ?
H01B C010 H01C 101(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_D-1ClNaAA
_audit_block_doi                 10.5517/ccdc.csd.cc23mgv2
_database_code_depnum_ccdc_archive 'CCDC 1955134'
loop_
_audit_author_name
_audit_author_address
'Jiaxi Liu'
;Jilin University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;
_audit_creation_date             2019-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H18 Cl2 O4, C4 H8 O'
_chemical_formula_sum            'C30 H26 Cl2 O5'
_chemical_formula_weight         537.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8413(5)
_cell_length_b                   6.6231(2)
_cell_length_c                   27.4197(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.7890(10)
_cell_angle_gamma                90
_cell_volume                     2512.40(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9711
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull whiteish colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            49795
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.666
_diffrn_reflns_theta_min         2.945
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5293
_reflns_number_total             5819
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         5819
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+1.4888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0766
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.20560(2) -0.22120(4) 0.29861(2) 0.01720(7) Uani 1 1 d . . . . .
Cl02 Cl 0.36435(2) -0.23578(4) 0.40613(2) 0.01702(7) Uani 1 1 d . . . . .
O003 O 0.17842(6) 0.57062(14) 0.47622(3) 0.02023(19) Uani 1 1 d . . . . .
O004 O 0.27037(6) 0.73647(13) 0.55292(3) 0.01803(18) Uani 1 1 d . . . . .
O005 O -0.03535(6) 0.07892(16) 0.43832(3) 0.0232(2) Uani 1 1 d . . . . .
O006 O 0.09755(6) 0.12437(15) 0.48553(3) 0.0217(2) Uani 1 1 d . . . . .
O007 O 0.30684(6) 0.36229(14) 0.47883(3) 0.02090(19) Uani 1 1 d . . . . .
C008 C 0.33059(8) 0.13257(17) 0.36621(4) 0.0123(2) Uani 1 1 d . . . . .
C009 C 0.48115(8) -0.04053(17) 0.34420(4) 0.0133(2) Uani 1 1 d . . . . .
C00A C 0.14489(8) 0.04209(18) 0.22822(4) 0.0130(2) Uani 1 1 d . . . . .
C00B C 0.08927(8) 0.33137(18) 0.29698(4) 0.0130(2) Uani 1 1 d . . . . .
C00C C 0.44357(9) 0.29689(18) 0.31250(4) 0.0157(2) Uani 1 1 d . . . . .
C00D C 0.13678(8) 0.09304(17) 0.36777(4) 0.0121(2) Uani 1 1 d . . . . .
C00E C 0.08005(8) 0.37436(18) 0.24815(4) 0.0141(2) Uani 1 1 d . . . . .
C00F C 0.05289(8) 0.14700(18) 0.44696(4) 0.0140(2) Uani 1 1 d . . . . .
C00G C 0.12749(8) 0.14464(17) 0.31414(4) 0.0117(2) Uani 1 1 d . . . . .
C00H C 0.50697(8) 0.12998(18) 0.31590(4) 0.0138(2) Uani 1 1 d . . . . .
C00I C 0.23282(8) 0.42163(18) 0.45939(4) 0.0149(2) Uani 1 1 d . . . . .
C00J C 0.09286(8) 0.25214(17) 0.40331(4) 0.0130(2) Uani 1 1 d . . . . .
C00K C 0.23848(8) 0.13963(17) 0.39363(4) 0.0120(2) Uani 1 1 d . . . . .
C00L C 0.15600(8) 0.00807(17) 0.27938(4) 0.0125(2) Uani 1 1 d . . . . .
C00M C 0.35810(8) 0.29648(18) 0.33635(4) 0.0146(2) Uani 1 1 d . . . . .
C00N C 0.19568(8) 0.34109(18) 0.41088(4) 0.0131(2) Uani 1 1 d . . . . .
C00O C 0.59607(9) 0.12775(19) 0.29141(4) 0.0174(2) Uani 1 1 d . . . . .
C00P C 0.10627(8) 0.23128(18) 0.21269(4) 0.0139(2) Uani 1 1 d . . . . .
C00Q C 0.39270(8) -0.03034(17) 0.36940(4) 0.0126(2) Uani 1 1 d . . . . .
C00R C 0.16735(8) -0.10396(19) 0.19235(4) 0.0168(2) Uani 1 1 d . . . . .
C00S C 0.54460(9) -0.20909(19) 0.34652(5) 0.0174(2) Uani 1 1 d . . . . .
C00T C 0.65589(9) -0.0361(2) 0.29453(5) 0.0198(2) Uani 1 1 d . . . . .
C00U C 0.15297(9) -0.0620(2) 0.14362(4) 0.0202(3) Uani 1 1 d . . . . .
C00V C 0.09443(9) 0.2715(2) 0.16179(4) 0.0182(2) Uani 1 1 d . . . . .
C00W C 0.62972(9) -0.2066(2) 0.32210(5) 0.0205(3) Uani 1 1 d . . . . .
C00X C 0.11726(9) 0.1278(2) 0.12821(4) 0.0216(3) Uani 1 1 d . . . . .
C00Y C 0.40087(9) 0.9542(2) 0.53541(5) 0.0223(3) Uani 1 1 d . . . . .
C00Z C 0.35671(10) 0.6376(2) 0.57168(5) 0.0219(3) Uani 1 1 d . . . . .
C010 C 0.29568(10) 0.9474(2) 0.55020(5) 0.0235(3) Uani 1 1 d . . . . .
C011 C 0.43876(10) 0.7389(2) 0.54541(5) 0.0248(3) Uani 1 1 d . . . . .
H00B H 0.0708(10) 0.435(2) 0.3193(5) 0.017(4) Uiso 1 1 d . . . . .
H00D H 0.1145(10) -0.044(2) 0.3719(5) 0.013(3) Uiso 1 1 d . . . . .
H00K H 0.2443(10) 0.052(2) 0.4220(5) 0.013(3) Uiso 1 1 d . . . . .
H00J H 0.0434(11) 0.341(2) 0.3888(5) 0.016(3) Uiso 1 1 d . . . . .
H00E H 0.0549(11) 0.505(2) 0.2380(5) 0.017(4) Uiso 1 1 d . . . . .
H00N H 0.2039(11) 0.451(2) 0.3869(5) 0.018(4) Uiso 1 1 d . . . . .
H00V H 0.0703(11) 0.403(3) 0.1518(6) 0.021(4) Uiso 1 1 d . . . . .
H00M H 0.3142(11) 0.411(2) 0.3331(5) 0.021(4) Uiso 1 1 d . . . . .
H00R H 0.1912(11) -0.234(2) 0.2031(6) 0.019(4) Uiso 1 1 d . . . . .
H00O H 0.6132(12) 0.243(2) 0.2723(6) 0.023(4) Uiso 1 1 d . . . . .
H00S H 0.5272(11) -0.327(3) 0.3645(6) 0.022(4) Uiso 1 1 d . . . . .
H00U H 0.1671(11) -0.164(3) 0.1199(6) 0.023(4) Uiso 1 1 d . . . . .
H00W H 0.6721(12) -0.322(3) 0.3245(6) 0.026(4) Uiso 1 1 d . . . . .
H00T H 0.7152(11) -0.038(2) 0.2772(6) 0.022(4) Uiso 1 1 d . . . . .
H00C H 0.4605(11) 0.407(3) 0.2932(6) 0.023(4) Uiso 1 1 d . . . . .
H01A H 0.2522(13) 1.008(3) 0.5265(6) 0.033(4) Uiso 1 1 d . . . . .
H01C H 0.4500(12) 0.668(3) 0.5147(7) 0.032(4) Uiso 1 1 d . . . . .
H00X H 0.1097(12) 0.154(3) 0.0935(6) 0.026(4) Uiso 1 1 d . . . . .
H00A H 0.4040(12) 0.990(3) 0.5011(6) 0.027(4) Uiso 1 1 d . . . . .
H00G H 0.3616(12) 0.665(3) 0.6073(6) 0.025(4) Uiso 1 1 d . . . . .
H00H H 0.3505(12) 0.492(3) 0.5648(6) 0.026(4) Uiso 1 1 d . . . . .
H01D H 0.4984(14) 0.736(3) 0.5645(7) 0.033(5) Uiso 1 1 d . . . . .
H01B H 0.2864(13) 1.007(3) 0.5839(7) 0.036(5) Uiso 1 1 d . . . . .
H00F H 0.4359(13) 1.057(3) 0.5541(6) 0.032(4) Uiso 1 1 d . . . . .
H005 H -0.0522(15) 0.009(3) 0.4633(8) 0.050(6) Uiso 1 1 d . . . . .
H003 H 0.2082(14) 0.625(3) 0.5015(7) 0.041(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00L 1.7414(12) . ?
Cl02 C00Q 1.7449(11) . ?
O003 C00I 1.3325(15) . ?
O003 H003 0.87(2) . ?
O004 C00Z 1.4432(15) . ?
O004 C010 1.4428(16) . ?
O005 C00F 1.3165(14) . ?
O005 H005 0.86(2) . ?
O006 C00F 1.2174(14) . ?
O007 C00I 1.2059(15) . ?
C008 C00K 1.5009(15) . ?
C008 C00M 1.4189(16) . ?
C008 C00Q 1.3806(16) . ?
C009 C00H 1.4221(16) . ?
C009 C00Q 1.4259(16) . ?
C009 C00S 1.4206(16) . ?
C00A C00L 1.4245(15) . ?
C00A C00P 1.4224(16) . ?
C00A C00R 1.4208(16) . ?
C00B C00E 1.3708(16) . ?
C00B C00G 1.4195(16) . ?
C00B H00B 0.958(15) . ?
C00C C00H 1.4127(16) . ?
C00C C00M 1.3694(16) . ?
C00C H00C 0.937(17) . ?
C00D C00G 1.5112(15) . ?
C00D C00J 1.5706(15) . ?
C00D C00K 1.5867(15) . ?
C00D H00D 0.966(15) . ?
C00E C00P 1.4133(16) . ?
C00E H00E 0.969(16) . ?
C00F C00J 1.5049(15) . ?
C00G C00L 1.3804(15) . ?
C00H C00O 1.4226(16) . ?
C00I C00N 1.5083(15) . ?
C00J C00N 1.5483(15) . ?
C00J H00J 0.979(15) . ?
C00K C00N 1.5403(16) . ?
C00K H00K 0.972(15) . ?
C00M H00M 0.972(16) . ?
C00N H00N 0.989(16) . ?
C00O C00T 1.3660(18) . ?
C00O H00O 0.962(17) . ?
C00P C00V 1.4252(16) . ?
C00R C00U 1.3732(17) . ?
C00R H00R 0.967(16) . ?
C00S C00W 1.3734(17) . ?
C00S H00S 0.961(17) . ?
C00T C00W 1.4124(19) . ?
C00T H00T 0.962(16) . ?
C00U C00X 1.410(2) . ?
C00U H00U 0.964(17) . ?
C00V C00X 1.3684(19) . ?
C00V H00V 0.968(16) . ?
C00W H00W 0.966(17) . ?
C00X H00X 0.971(17) . ?
C00Y C010 1.5241(18) . ?
C00Y C011 1.541(2) . ?
C00Y H00A 0.972(17) . ?
C00Y H00F 0.971(19) . ?
C00Z C011 1.520(2) . ?
C00Z H00G 0.994(17) . ?
C00Z H00H 0.989(18) . ?
C010 H01A 0.960(18) . ?
C010 H01B 1.017(19) . ?
C011 H01C 0.980(18) . ?
C011 H01D 0.965(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00I O003 H003 108.7(13) . . ?
C010 O004 C00Z 104.95(10) . . ?
C00F O005 H005 108.2(14) . . ?
C00M C008 C00K 120.84(10) . . ?
C00Q C008 C00K 121.98(10) . . ?
C00Q C008 C00M 117.17(10) . . ?
C00H C009 C00Q 117.45(10) . . ?
C00S C009 C00H 118.88(10) . . ?
C00S C009 C00Q 123.67(11) . . ?
C00P C00A C00L 117.53(10) . . ?
C00R C00A C00L 123.70(11) . . ?
C00R C00A C00P 118.74(10) . . ?
C00E C00B C00G 121.80(11) . . ?
C00E C00B H00B 117.3(9) . . ?
C00G C00B H00B 120.9(9) . . ?
C00H C00C H00C 118.8(10) . . ?
C00M C00C C00H 120.73(11) . . ?
C00M C00C H00C 120.4(10) . . ?
C00G C00D C00J 115.42(9) . . ?
C00G C00D C00K 116.00(9) . . ?
C00G C00D H00D 107.9(8) . . ?
C00J C00D C00K 86.98(8) . . ?
C00J C00D H00D 115.3(8) . . ?
C00K C00D H00D 114.4(8) . . ?
C00B C00E C00P 120.97(11) . . ?
C00B C00E H00E 119.2(9) . . ?
C00P C00E H00E 119.9(9) . . ?
O005 C00F C00J 112.16(10) . . ?
O006 C00F O005 123.87(11) . . ?
O006 C00F C00J 123.96(10) . . ?
C00B C00G C00D 122.62(10) . . ?
C00L C00G C00B 116.98(10) . . ?
C00L C00G C00D 120.40(10) . . ?
C009 C00H C00O 119.05(11) . . ?
C00C C00H C009 119.42(10) . . ?
C00C C00H C00O 121.53(11) . . ?
O003 C00I C00N 112.75(10) . . ?
O007 C00I O003 124.73(11) . . ?
O007 C00I C00N 122.41(11) . . ?
C00D C00J H00J 115.6(9) . . ?
C00F C00J C00D 110.01(9) . . ?
C00F C00J C00N 115.38(9) . . ?
C00F C00J H00J 109.4(9) . . ?
C00N C00J C00D 88.08(8) . . ?
C00N C00J H00J 116.9(9) . . ?
C008 C00K C00D 121.71(9) . . ?
C008 C00K C00N 121.44(10) . . ?
C008 C00K H00K 109.3(8) . . ?
C00D C00K H00K 107.0(8) . . ?
C00N C00K C00D 87.79(8) . . ?
C00N C00K H00K 107.2(8) . . ?
C00A C00L Cl01 117.75(9) . . ?
C00G C00L Cl01 118.74(8) . . ?
C00G C00L C00A 123.50(10) . . ?
C008 C00M H00M 118.1(9) . . ?
C00C C00M C008 121.90(11) . . ?
C00C C00M H00M 120.0(9) . . ?
C00I C00N C00J 122.64(9) . . ?
C00I C00N C00K 116.96(10) . . ?
C00I C00N H00N 106.5(9) . . ?
C00J C00N H00N 108.3(9) . . ?
C00K C00N C00J 89.42(8) . . ?
C00K C00N H00N 112.3(9) . . ?
C00H C00O H00O 118.7(10) . . ?
C00T C00O C00H 120.76(12) . . ?
C00T C00O H00O 120.5(10) . . ?
C00A C00P C00V 119.25(11) . . ?
C00E C00P C00A 119.14(10) . . ?
C00E C00P C00V 121.61(11) . . ?
C008 C00Q Cl02 119.67(9) . . ?
C008 C00Q C009 123.28(10) . . ?
C009 C00Q Cl02 117.05(9) . . ?
C00A C00R H00R 118.5(9) . . ?
C00U C00R C00A 120.49(12) . . ?
C00U C00R H00R 121.0(9) . . ?
C009 C00S H00S 119.9(9) . . ?
C00W C00S C009 120.48(12) . . ?
C00W C00S H00S 119.6(9) . . ?
C00O C00T C00W 120.23(11) . . ?
C00O C00T H00T 120.4(10) . . ?
C00W C00T H00T 119.4(10) . . ?
C00R C00U C00X 120.72(12) . . ?
C00R C00U H00U 119.3(10) . . ?
C00X C00U H00U 120.0(10) . . ?
C00P C00V H00V 118.2(9) . . ?
C00X C00V C00P 120.46(12) . . ?
C00X C00V H00V 121.3(9) . . ?
C00S C00W C00T 120.59(12) . . ?
C00S C00W H00W 119.1(10) . . ?
C00T C00W H00W 120.3(10) . . ?
C00U C00X H00X 118.5(10) . . ?
C00V C00X C00U 120.30(11) . . ?
C00V C00X H00X 121.2(10) . . ?
C010 C00Y C011 104.36(11) . . ?
C010 C00Y H00A 109.6(10) . . ?
C010 C00Y H00F 110.2(10) . . ?
C011 C00Y H00A 111.9(10) . . ?
C011 C00Y H00F 113.1(11) . . ?
H00A C00Y H00F 107.6(15) . . ?
O004 C00Z C011 104.69(10) . . ?
O004 C00Z H00G 107.3(10) . . ?
O004 C00Z H00H 108.1(10) . . ?
C011 C00Z H00G 110.8(10) . . ?
C011 C00Z H00H 113.8(10) . . ?
H00G C00Z H00H 111.8(14) . . ?
O004 C010 C00Y 106.14(11) . . ?
O004 C010 H01A 106.9(11) . . ?
O004 C010 H01B 106.9(11) . . ?
C00Y C010 H01A 113.0(10) . . ?
C00Y C010 H01B 112.3(10) . . ?
H01A C010 H01B 111.1(15) . . ?
C00Y C011 H01C 110.5(11) . . ?
C00Y C011 H01D 113.3(11) . . ?
C00Z C011 C00Y 103.75(11) . . ?
C00Z C011 H01C 109.8(11) . . ?
C00Z C011 H01D 111.9(11) . . ?
H01C C011 H01D 107.6(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
